40 Strategy Blog

High-stakes initiatives fail more than 80% of the time, yet leaders still have to pursue them to grow. In this episode of the Measure Success Podcast, Carl J. Cox talks with John Rossman, former Amazon executive and author of Big Bet Leadership, about how leaders should approach bold, risky transformation efforts in the age of AI. John shares why leaders must stop chasing predictability, treat strategy as a set of hypotheses, and focus on one critical bet at a time. The discussion covers AI strategy, experimentation, leadership discipline, and how organizations avoid dilution of focus. This episode is for executives, operators, and entrepreneurs responsible for leading real change. 🎧 Listen now and measure success differently. John Rossman Links:  LinkedIn https://www.linkedin.com/in/john-rossman/   Facebook https://www.facebook.com/rossmanpartners Website http://rossmanpartners.com/ Check out this episode!

AI is everywhere, but most businesses are using it the wrong way. In this episode of the Measure Success Podcast, Carl J. Cox sits down with Eli Portnoy, co-founder and CEO of BackEngine.ai, to talk about the real gap between AI hype and real-world results. Eli explains why generic AI outputs fail, why context matters more than tools, and how sales and go-to-market strategies must evolve in a crowded, low-trust environment. They also discuss how outbound sales has changed, why easy channels stop working, and what leaders can do today to build relevance, trust, and long-term growth. If you want a clear, practical conversation about AI, strategy, and modern business execution, this episode delivers. Listen now and learn how to apply AI with intention. https://www.linkedin.com/in/eliportnoy/ https://www.backengine.com/ Check out this episode!

This episode is sponsored by Altezza Solutions , liberating entrepreneurs through fractional sales execution. Today, Steve helps growth-stage companies break through revenue barriers while giving founders the freedom to focus on building extraordinary businesses.   Founder-led businesses often grow fast, then stall. In this episode of the Measure Success Podcast, Carl Cox sits down with Steve Caton, Founder and CEO of Altezza Solutions, to discuss why sales becomes the biggest bottleneck for growing companies. Steve shares why hiring salespeople often fails, how founders unintentionally trap themselves in the sales role, and what it takes to build repeatable, predictable sales systems. You’ll learn: Why sales talent alone does not solve growth How systems and process drive consistency When fractional sales makes sense How founders can step out of the sales seat If sales depends on you, growth will too. Listen now and measure what success really looks like....

Selling to private equity is not the end of the journey. It is the beginning of a new phase of growth. In this episode of the Measure Success Podcast, Carl J. Cox, CEO of 40 Strategy and 40 Accounting sits down with Neel Bhargave, founding partner at NB Group, to unpack how private equity partnerships really work for founder- and family-owned businesses. Neel shares how his firm approaches growth-focused investing, why rolling equity is critical, and how conservative use of debt protects long-term value. The conversation also explores what typically changes in the first 18 months after an investment, including finance, leadership structure, and strategic planning. This episode offers clear insight for founders thinking about private equity and operators preparing for their next stage of scale. Listen now and learn how to build a business that is ready for growth, partnership, and long-term success.   Check out this episode!

In this episode of the Measure Success Podcast, Carl J Cox sits down with real estate investor and educator Jay Conner to break down private money and why it has been the foundation of his business since 2009. Jay explains how private money works, who private lenders really are, and why having capital ready changes everything about deal execution. He shares a real world case study where preparation and access to funding made a fast, profitable exit possible when traditional financing would have failed. Listeners will learn why mindset matters as much as mechanics, how conservative strategy protects both sides, and why serious operators stop chasing money and start attracting it. If you want more control, less friction, and a cleaner path to growth, this episode delivers a practical framework worth studying. Listen now and learn how strategy shapes results.   Check out this episode!

In this episode of the Measure Success Podcast, Carl J. Cox sits down with John Whitt, founder of Business Whitt and author of Checkmate, to explore how strategic thinking, leadership, and generosity intersect. John explains how lessons from competitive chess apply directly to business. Small advantages, disciplined execution, and resource placement matter more than chasing quick wins. The conversation covers clarity in goal setting, identifying constraints, testing ideas before scaling, and leading with generosity as a competitive edge. Listeners will gain practical insight into building strategy that holds up under pressure and leadership habits that create lasting results. Listen now and learn how to think ahead, execute with intention, and lead in a way that drives sustainable success.   Check out this episode!